chapter – i - shodhganga : a reservoir of indian theses...
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CHAPTER – VI
References and summary
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SUMMARY
Page 225
SUMMARY
Any substance that is carefully used for diagnosis, cure and
prevention for altering the structure and function of the body is called drug. In
the modern era, drugs play an important role in the progress of human
civilization. While primitive man depended mainly on plant product and metal
salts to cure diseases, modern man uses a wide range of synthetic organic
compounds and biotechnology- derived antibiotics, vaccines, etc. There are
many important stages before a compound is used as a drug. The three
important stages in the use of a drug as a medicine, i.e., the conversion of a
drug into a formulation are i. The discovery of the drug. ii. The
manufacture of the drug in bulk form. iii. The formulation of a drug into
different dosage forms like tablet, capsule, injection, syrup etc. First
stage is the drug discovery, where the compounds are screened for biological
activities. Second stage is the manufacture of the drug using well understood
chemistry and adapting safe and proper manufacturing and analytical
practices and the third stage is the formulation of the drug in a convenient
dosage. Chemists play an important role in pharmaceutical research, as they
synthesize, purify and analyze the drugs. The study of conversion of drugs
into medicine and its manufacture, stability and the effectiveness of the drug
dosage form is termed as pharmaceutics. The preparation, chemical and
physical composition, reactive nature, geometry, influence on an organism,
quality control methods, storage conditions and like which are pre-requisites
in the study of drugs fall under pharmaceutical chemistry, a potential field,
based on the general laws of chemistry.
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Pharmaceutical analysis deals not only with drugs and their
formulations but also with their precursors. However, degree of purity and the
quality of medicament is a must. The quality of a drug is decided only after its
authenticity is tested, that too in the drug and its formulations. Whatever may
be the application, quality is paramount as it is more vital in the field of
medicine as the target is life. The growth of pharmaceutical industry, increase
in the number and variety of drugs and availability of sophisticated
instruments has paved way for rapid progress in providing simple analytical
procedures for the analysis of complex formulations also. The time tested
assays of medicinal products are no doubt still dependable. The availability of
new techniques with improved equipments has made the latest techniques
attractive.
Several methods for the estimation of drugs are classified into
physical, chemical, physico-chemical and biological ones. Physical methods
involve the study of the physical properties such as solubility, transparency or
degree of turbidity, color density, specific gravity etc. Physico-chemical
methods involve the study of the physical phenomena that occurs as a result
of chemical reactions [16-18]. These include optical and chromatographic
methods. The combination of mass spectroscopy with gas chromatography is
one of the most powerful tools available. The chemical methods include the
gravimetric and volumetric procedures which are based on complex
formation, redox reactions etc. Titration in non-aqueous media and
complexometry are also being used in pharmaceutical analysis. The
continuous growth of new drugs needs new methods for controlling the
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quality. Modern pharmaceutical analytical techniques need the following
requirements.
i. Minimal time for analysis
ii. Analysis accuracy should satisfy the demands of pharmacopoeia
iii. Analysis should be economical
iv. The selected method should be precise and selective
v. The above requirements are met by the physico-chemical methods of
analysis. An advantage is their universal nature that can be employed for
analyzing organic compounds with any diverse structure. Visible
spectrophotometry is generally preferred especially by small scale industries
as the cost of the equipment is less and the maintenance problems are
minimal.
Visible spectrophotometry and HPLC techniques have been
used in the present thesis work. Using visible spectrophotometry, seventeen
new analytical methods are developed for the assay of three selected drugs {
Saquinavir [SQVR], Atomoxetine [ATXT], Duloxetine [DLXT]} (Table A,
Page 181) by exploiting their functional groups present in them with the use of
appropriate chromogenic reagents in pure form and pharmaceutical
formulations (Table B, Page 182 & 183). In addition to visible
spectrophotometric methods, the author has developed one new HPLC
procedures for the assay of the selected drugs {Oseltamivir [OTVR]} in
pharmaceutical formulations (Table C, Page 184).
The content of the thesis has been divided into five chapters and
appropriate references have been placed at the end.
Page 228
Chapter-I starts with an introduction giving a brief account of various
aspects considered for the development of new visible spectrophotometric
(Part-A) and HPLC (Part-B) methods for the assay of four selected drugs.
The information given under Part-A, the chemistry of chromogenic reagents,
and the reactions used in the present investigation, and the general
methodology for developing new visible spectrophotometric methods (spectral
characteristics of the colored species) optimization of experimental conditions
(effect of pH, reagent concentration and order of addition, keeping time and
temperature during each addition, effect of solvent, color development and
stability) optical characteristics (Beer’s law limits, Sandell’s sensitivity,
optimum photometric range and molar absorptivity useful for sensitivity),
selectivity, precision, standard deviation, percent range of error, testing of
significance by F-test, accuracy( comparison of the proposed and reference
methods of pharmaceutical formulation, testing of significance by t-test and
recovery experiments in the present investigations.
The information given under Part-B, includes HPLC system
components (solvent delivery systems, solvent degassing systems, gradient
elution devices, sample introduction systems liquid chromatography detectors,
column packing materials inclusive of bonded phase, derivatization, gradient
elution), performance calculations (relative retention, theoretical plates, plates
per meter, height equivalent to theoretical plate, capacity factor, resolution,
peak asymmetry), linear fit properties of solvents used in chromatography and
Page 229
validation of analytical methods(recovery, response function, sensitivity,
precision and accuracy) in the present investigations.
Chapter - II, begins with the introduction giving brief account of
chemical name, structure, and mode of action, characteristics, analytically
useful functional groups, commercially available formulations and literature on
physicochemical methods reported for Saquinavir [SQVR]. Yet no visible
spectrophotometric method has been developed for the assay of SQVR in
pharmaceutical formulations. The chemical features of analytically useful
functional groups in SQVR offer a lot of scope for the development of new
methods, hopefully with better sensitivity precision and accuracy, which
prompted the author to carry out investigations in this accord. The author has
developed nine versatile visible spectrophotometric methods for the assay of
SQVR in pure and Pharmaceutical dosage forms
Saquinavir [SQVR] possesses different functional groups such as
aromatic primary amine and keto groups of varied reactivity. The primary
amine in Saquinavir [SQVR] was responsible for the development of ion-
association complex formation with acid dyes such as Bromo thymol
blue (BTBP) [M1a] and Bromo phenol blue (BPB) [M1b], condensation
reaction with Isatin - H2SO4 [M2]; Xanthydrol-H2SO4 [M3] and Vanillin-
H2SO4 [M4]; PDAB [M6]; PDAC [M6]; Ninhydrin in presence of ascorbic
acid [M7]; and diazo coupling product with Phloroglucinol and Resorcinol
[M8 and M9].
Page 230
Chapter - III, opens with the introduction giving or brief account of
chemical name, structure, therapeutic importance, analytically useful
functional groups, commercially available formulations and the literature on
the physicochemical methods reported so far for Atomoxetine [ATXT]. This
chapter describes the author’s attempts in developing visible
spectrophotometric methods as there is only one visible spectrophotometric
method for the assay of Atomoxetine [ATXT] in the literature survey and
hence, there is a need to develop few more visible spectrophotometric
methods for its determination in pharmaceutical dosage forms. Based on this
the author proposed five visible spectrophotimetric methods by exploiting the
functional groups present in it.
Atomoxetine [ATXT] possesses secondary amine group. The five
methods proposed by the author are based on reactivity of secondary amine
with various reagents. Oxidative coupling reactions with MBTH in presence
of IO4- / Fe (III) oxidant [M10 and M11], with Brucine in the presence of IO4
-
oxidant [M12] and redox reaction with Fe (III) in the presence of [Fe(CN)6]-3
[M14] and with AV [M15].
Chapter - IV of this chapter is focused on the author attempts in
developing suitable visible spectrophotometric methods with better sensitivity,
selectivity, precision and accuracy by exploiting the analytically useful groups
in Duloxetine [DLXT], the author developed four visible spectrophotometric
methods for Duloxetine [DLXT].
Page 231
The secondary amine of Duloxetine [DLXT] forms Oxidative
coupling reactions with Brucine in the presence of IO4 - oxidant [M12] and
with DCQC [M13]; charge transfer complex formation with DDQ [M16] and
DHQ [M17].
Chapter - V, reveals a brief note on the chemical properties and the
literature survey of the HPLC methods on Oseltamivir [OTVR]. As there are
very few HPLC (especially in pharmaceutical formulations) methods for the
assay of Oseltamivir [OTVR] were reported in the literature and therefore the
author has attempted to developed a simple HPLC method for the
quantitative estimation of Oseltamivir [OTVR] with a better sensitivity by
using stationary phase [YMC Pack Pro C18 RS, 250mm x 4.6 mm, 5m]
and mobile phase combination of [solution A and solution B in the ratio of
75:25 v/v], where solution A is Phosphate buffer solution, solution B is
Acetonitrile. The detection was carried at 220nm. The results of this
investigation are incorporated in this part of this chapter
The data and information of selected drugs, reagents and techniques
given in chapters [II-V] (Table - B & C, Page 182-184) reveals that the
proposed methods are simple, selective, sensitive (some are superior to most
of the reported visible spectrophotometric methods) and accurate with
reasonable precision and accuracy. In addition, selectivity to each selected
drug and its formulations was achieved by selecting the appropriate
combination of solvent systems in the sample solution preparation and
Page 232
exploring specific functional groups exclusively present in the drug. The
proposed methods can be used as alternative methods to reported ones and
provide wide choice for the routine determination of the above mentioned
drugs depending upon the availability of chemicals and situation arising due
to the presence of concomitants. Three papers were in press for publication
and much of the work has been communicated to reputed national and
international journals.
Page 233
TABLE - A
STRUCTURAL FEATURES OF SELECTED DRUGS
SI. No
Generic Name Structure
Drug Category
Chemical Name, Molecular formula& Molecular
weight
Analytical important
moieties/functional groups
1 Saquinavir
Antiviral N-tert-butyl-decahydro-2-[2(R)-hydroxy-4-phenyl-
3(S)-[[N-(2quinolylcarbonyl)-L-
asparaginyl]amino]butyl]-(4aS,8aS)-isoquinoline-
3(S)-carboxamide
Molecular Formula: C38H50N6O5
Molecular weight: 670.86 g mol−1
Primary, Tertiary nitrogen and
keto group
2 Atomoxetine
Antideptrssive N-methyl-3-phenyl-3-(o-tolyloxy)-propylamine
hydrochloride
Molecular Formula: C16H13Cl2NO4 .
Molecular weight: 291.82 g mol−1
secondary nitrogen group
3 Duloxetine
Antidepressive (+)-(S)-N-methyl-(1-naphthyloxy)-2-
thiophenepropylamine hydrochloride[
Chemical Formula: C18H19NOS,
Molecular weight: 297.41
secondary nitrogen group
4
Oseltamivir
phosphate
Antiviral (3R,4R,5S)-4-acetylamino-5-amino-3-(1-
ethylpropoxy)-1-cyclohexene-1-carboxylic acid,
ethyl ester
Chemical Formula: C16H31N2O8P
Molecular weight: 538.13
Carboxylic and secondary
nitrogen group
Page 234
TABLE - B LIST OF PROPOSED VISIBLE SPECTROPHOTOMETRIC METHODS
Type of Reaction Reagent used for the
exploitation of functional
group/ moiety
Method
proposed in
the thesis
Drug responded max nm max
L.mole-1 cm-1
Beer’s law limits
g ml-1 References
Ion association
complex
BTB M1 a SQVR 465 1.811 x 104 3.0 – 15.0 Chapter II, present work
Ion association
complex
BPB M1b
SQVR 615 1.077 x 104 3.0 – 15.0 Chapter II, present work
Condensation Isatin - H2SO4 M2
SQVR 630 3.045 x 104 2.0 – 10.0 Chapter II, present work
Condensation Xanthydrol - H2SO4 M3
SQVR 660 5.890 x 104 2.5 – 12.5 Chapter II, present work
Condensation Vanillin M4
SQVR 535 1.650 x 105 2.0 – 10.0 Chapter II, present work
Condensation PDAB M5
SQVR 540 4.243 x 104 2.0 – 10.0 Chapter II, present work
Condensation PDAC M6
SQVR 470 5.172 x 104 2.0 – 10.0 Chapter II, present work
Condensation Ninhydrin – Acsorbic acid M7
SQVR 560 1.224 x 104
4.0 – 20.0 Chapter II, present work
Diazo coupling NaNO2-phloroglucinol M8 SQVR 520 8.153 x 105
4.0 – 20.0 Chapter II, present work
Diazo coupling NaNO2-resorcinol M9
SQVR 625 9.397 x 105 4.0 – 20.0 Chapter II, present work
Page 235
TABLE - B
LIST OF PROPOSED VISIBLE SPECTROPHOTOMETRIC METHODS
Type of Reaction
Reagent used for the
exploitation of functional
group/ moiety
Method
proposed in
the thesis
Drug responded max nm max
L.mole-1 cm-1
Beer’s law limits
g ml-1 References
Oxidative Coupling MBTH - NaIO4 M10 ATXT 585 5.132 x 105 4.0 – 20.0 Chapter III, present work
Oxidative Coupling MBTH - Fe(III) M11 ATXT 625 3.600 x 105 2.0 – 10.0 Chapter III, present work
Oxidative Coupling Brucine - IO4- M12 ATXT 520 1.264 x 104 2.5 – 12.5 Chapter III, present work
Oxidative Coupling Brucine - IO4- M12 DLXT 520 1.683 x 104 2.5 – 12.5 Chapter IV, present work
Oxidative Coupling DCQC M13 DLXT 470 4.297 x 105 4.0 – 16.0 Chapter IV, present work
Redox Reaction Fe(III)/[Fe(CN)6]-3 M14 ATXT 650 5.694 x 105 5.0 – 25.0 Chapter III, present work
Redox Reaction AV-H2SO4 M15 ATXT 740 5.321 x 105 5.0 – 25.0 Chapter III, present work
Charge Transfer
reaction
DDQ M16 DLXT 480 6.632 x 105 2.5 – 12.5 Chapter IV, present work
Charge Transfer
reaction
CA –M eOH M17 DLXT 490 1.549 x 104 2.5 – 12.5 Chapter IV, present work
Page 236
TABLE - C
RP-HPLC METHODS
Drug responded Chromatographic column
used Mobile phase composition Detection limit Linearity range Reference
Oseltamivir phosphate
YMC Pack Pro C18 RS,
250mm x 4.6 mm, 5m
Combination of phosphate buffer
of pH 2.5 and acetonitrile in the
ratio of 75:25 v/v
220 0.08 -0.12mg.ml-1
Chapter - V